Dean's Day of Fun
by romancelover42
Summary: Dean spends the entire day making Sam beg for orgasm and teasing him by fingering and toys and some sexual verbal teasing


Dean's Day of Fun

Lying on the bed fully clothed next to Sam who was naked bound, blindfolded and tied up for him, at ten in the morning, he took in every bit of his precious baby brother like this.

This was punishment to get him off that demon blood and if he refused, he would be tortured further.

He raised Sam's bound knees up a bit, and says, "Relax baby boy, I'm gonna make it so good for you baby just take it for me. See how long you can take it."

Dean knows that more than anything he can drag this out of Sam for hours, and that Sam liked it agonizingly slowly. His little brother loved to be tortured, brought to the edge and teased.

Glancing toward his brother's inner thighs toward his swelled cock he watched the little cock cage rise and fall with Sam's increasing arousal.

Moving slowly he stroked, teased and tickled Sam's chest, face, neck, tugging his earlobes, running playful knuckles in different directions over his brother's ticklish tummy.

He toyed with Sam's nipples and runs fingers over his thighs, his soles slowly wiggling his fingers and tickling them.

Again watching the cage rise and fall, seeing his baby brother's cock grow, as cum began to leak, he ignored it, continuing to torture his little brother with pleasure.

Reaching down after a while, he began palming Sam's soft cock trapped in its little cage, toying with it fondly.

Leaning in he whispered seductively, "Still can't believe you let me do this to you baby boy. To your sexy body all mine. Love you like this naked and bound, blindfolded, and all spread out at my mercy."

Teasing fingers raked agony over his bound testicles.

Continuing whispering filthy things in Sam's ear, Dean said, "Love your soft little cock how vulnerable and pretty it looks for me. So fucking hot like this, Sam, you have no idea. Make you take it."

Sam moaned at the pleasure and Dean grinned wickedly.

Going across with one hand he softly agonizingly slowly brushed Sam's underarms with his fingertips, with the other he felt two of Dean's fingers slip inside of him, quivering with the torment.

Brushing Sam's insides while slowly tickling and teasing him Dean whispered, "Buy you a big dildo, a vibrator, a butt plug, record me teasing you, bringing you to the edge as many times as I want and you just lying on the bed taking it. Begging and pleading to let you cum."

Dean licked Sam's ticklish armpit as Sam wailed, panted, begged moving his hips in circles rutting against Dean's cock.

"Gonna cum for me Sammy? Come with just my fingers up your ass?"

Sam begged, "Please Dean please."

Dean stopped moving his fingers for a moment, but kept them tight inside Sam, again licking and tickling Sam's underarms again and again, his cock leaking steady drops of precum soaking against Dean's pants.

Feeling him shake and shiver, chuckling darkly he said, "Christ so sensitive aren't you little Sammy?"

Keeping him still he warned, "Don't move Sammy, just take it."

Sam swallowed hard, nodding.

Adding a finger with the other two, Dean worked his brother slowly, so agonizingly slowly, Sam moaned.

"I like it when you beg me to let you cum."

"Please, Dean. Please."

"So fucking beautiful like this Sammy, all spread out, tied eagle for me, naked, blindfolded, ticklish and begging."

Dean grinned mockingly as he teased, "I wonder how long you can take it Sammy."

Sam sobbed as Dean moved his fingers relentlessly inside Sam sending pleasuring shivers through him.

Leaning in Dean chuckled at his brother whispering, "Don't you love this Sammy? Me keeping you on edge like this all the time how long can you take the torture?"

He meanwhile pressed teasingly against the spongy flesh of his little brother's prostate then reinserted only two fingers, massaging and teasing Sam's prostate with more delicacy.

Placing his fingers ever so gently along the outer edge, rubbing it back and forth slowly between his fingers, so slowly, as Sam gasped, begged, and trembled.

"How long can you take it for me Sammy?"

Fingers teasing relentlessly again as he continued tickling Sam lightly, sending waves of pleasure and shivers through Sam.

"I feel it Sammy. How bad you want to cum."

Sam's cock was tortured through the cock cage leaking steadily, so wet, so hard.

Moving Sam's legs up slightly, Dean said, "Lift up my baby."

Sam lifted his back up arching slightly unable to receive any contact at all.

Dean taunted, "There you go. Hold yourself up. Just take it. Take it for me Sammy."

Sam wailed again as Dean licked his ticklish armpits and lightly scratching with one hand, and Dean chuckled, "The way you sound when I do this to you."

Continuing to tease Sam's prostate massaging it slowly, making sure Sam kept his back up, so he would not get any direct contact at all on his sensitive cock.

Dean teased, stroked, tickled, sucked, and licked until Sam's hair was damp from sweat with desperation.

Slowly lowering Sam's legs allowing him to lie back on the bed and relax for a moment, he reached over to grab a toy, teasing as he flicked it on, seeing recognition on Sam's face.

Grinning wickedly when Sam swallowed hard realizing it was a vibrator with little bumps on it.

Dean eased the toy into Sam's stretched hole and gave it a little nudge.

"So tight and hot little brother, gonna get this toy so far up your ass that you won't walk straight for a month." Dean teased wickedly

Turning it slightly, Dean continued, "Then, I'm gonna turn it on and watch you just fuck yourself on it and you'll be begging me to let you cum but nope, that's not happening until you beg for me and not that demon blood. We can be here all night if need be. And if you're not a good boy for me Sammy, I won't let you move at all, and it's just gonna be this thing hitting, stroking, teasing and tickling your prostate all night long."

Teasing Sam tickling him with his other hand softly, he flicked the switch to the lowest setting before pulling back and watching.

Sam jerked and gasped as the device hit that sweet spot since Dean had angled it so every time his brother moved, it would hit that one spot inside that drove Sam crazy.

The tip of the toy struck his prostate with every thrust as Sam begged and sobbed for release.

Feeling Dean's hand lightly, softly, tickle torturing and caressing over his tummy teasing him, it just enflamed Sam's desire more.

After about an hour of teasing Sam with the vibrator, Dean gripped it to slide it out being careful to leave it on so the little nubs rubbed and teased his little brother's entire length.

Cleaning it up, he stroked his brother's thigh teasingly and whispered, "Not done yet baby boy, gonna take you apart with another toy in my tool box."

Reaching under, Dean began running a slow torturous slick hand down the crack of his brother's ass.

That slick hand went on to cup and tease his balls and his hardening cock and felt Sam surrender with a groan.

"I'm going to have you begging Sammy." Dean ran his light tickling fingers back up Sam's ass, teasing out another gasp from Sam.

Sam felt something against his ass and whispered, "Oh god."

The thing was tracking across his butt lined up with his ass and smoothly inserted.

Sam's voice went hoarse as his ass tried to pull away from it, and clamp down on it at the same time.

Dean watched his brother with an evil glint his eye and thought, 'Sam was never more beautiful than when he was completely at his mercy.'

He was fighting the desire to just fuck his brother mercilessly now.

Dean ran the flat of one hand ghosting over his brother's ticklish ass, while twisting the butt plug excruciatingly slowly with the other one.

He knew with every sound that came from his little brother that he was definitely enjoying this, but Sam was at his mercy.

Dean loved doing this to his brother, creating the challenge of pushing Sam to his limits or beyond and make sure to string Sammy out so completely that he didn't know anything but the pleasure.

Teasingly he continued to play with the plug with one hand while lightly tickling up Sam's shivering spine.

"Dean." Sam moaned.

Leaning in he whispered, "What do you want baby brother?"

Not getting anything from Sam he moved back and pulled the plug out almost completely before re-angling it and pushing it back in.

"Tell me Sammy." Dean commanded sliding the plug a little away, refusing to give Sam that same stimulation again.

"Tell me what you want baby boy." Dean cooed teasingly.

"More." He heard Sam moan so Dean moved the plug just a little and heard, "please."

He pulled the plug out to tease him so that it was just at the very tip and waited.

There was a small whine from Sam and the way Sam's ass wiggled to try to regain the plug sent messages to Dean's body.

Running his fingers teasingly down Sam's ticklish back Dean pushed the plug back in sliding around to find his sweet spot.

Sam pulled at the restraints and made Dean grin widely and rewarded Sammy by stroking his hand down and between his brother's legs and skirting his fingers over Sam's sensitive balls.

He continued to tease and play a little bit longer pulling the plug out and sliding it back in with different speeds and different angles watching Sam writhe and moan.

Pulling it out slightly he gave Sam a slight spank and said, "Patience Sammy."

Having left it in the cooler earlier he knew the silicon rubber was cold and it made him shiver to think what it had to feel like.

He knew that to Sam with so different from body temperature that he had to be able to feel every last millimeter inside him.

Again he slipped the head of the plug into Sam's ass and wrapped his cold fingers around Sam's erection in unison.

"God. Dean. Hell."

He grinned at the sight of breaking Sam down to monosyllables.

Leaning in he whispered wickedly, "You like that don't you Sammy, you like that a lot" as he moved the plug and fisted Sam's cock firmly.

He set about working the plug slowly, loosening Sam with every pass, as he teased Sam's cock with his other hand.

Dean knew he had to be driving his brother crazy as he alternated the attacks making sure there was enough sensation to keep his arousal climbing, but not enough to make him cum.

He knew exactly what to do in order to thwart what Sammy was after.

Listening to Sammy he relished torturing his little brother, all about the control.

"Please." Sam begged.

Dean felt a lush of desire as Sam began to break down and come undone.

Enjoying every torturous moment he teased, "I can't hear you Sammy, what was that?"

"Please, Dean." Sam tried to lift his voice up a bit, but the request was vague.

Pushing the plug the last few millimeters so it slipped completely into Sam's ass he asked, "Please what Sammy?"

Dean encouraged, "You want to cum don't you Sammy?" as he twisted the plug around inside of Sam.

"Yes." Sam's voice was quiet and desperate.

He began working on Sam's cock this time, pulling the plug out slightly hearing Sam moan he just grinned in victory.

He re-angled the plug teasingly, and thumbed the head of Sam's cock with the other hand.

"You know what you have to do Sammy as he continued to tease Sam's cock relentlessly."

Dean glanced at the clock seeing it was now 2 PM he could let him knock out for a while make him scream his name.

He moved the plug as he could see Sam was on the edge of orgasm while trying to stay still, moving both hands in unison this time aiming for maximum sensation.

Sliding the cock cage off, Dean worked him hard and fast and his whole body began to shudder and shake as he screamed his name.

He milked Sam for every last drop, and spasm.

He finally decided to have mercy and slowly pulled the plug out. The whine that came from Sam made him smile even more.

The big brother loved Sam like this, so undone, and yet ready for more. And there would be more torture to come.


End file.
